1,3-Benzodioxol-5-amine → N4-(1,3-benzodioxol-5-yl)-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

HRID 63151

Reaction equation

HRID 63151 reaction equation
C1(N[C:7]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[N:8]=2)CCCC1.[O:23]1[C:27]2[CH:28]=[CH:29][C:30]([NH2:32])=[CH:31][C:26]=2[O:25][CH2:24]1>>[O:23]1[C:27]2[CH:28]=[CH:29][C:30]([NH:32][C:7]3[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]([NH:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)[N:8]=3)=[CH:31][C:26]=2[O:25][CH2:24]1

Participants

3

Reactant 2

HCID 843101,3-Benzodioxol-5-amineHCID 71738410N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Product 1

HCID 71738744N4-(1,3-benzodioxol-5-yl)-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine

Procedure

The titled compound was synthesized according to the procedure described for preparation of N4-cyclopentyl-5,6-dimethyl-N2-(pyridin-2-ylmethyl)pyrimidine-2,4-diamine (Example 29) using 1,3-benzodioxol-5-amine instead of cyclopentanamine. The crude material was purified by column chromatography eluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1), and then the final product was washed with diethyl ether to afford the titled compound as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm 2.04 (s, 3H), 2.32 (s, 3H), 4.69 (d, J=4.2 Hz, 2H), 5.76 (bs, 1H), 5.95 (s, 2H), 6.22 (s, 1H), 6.67-7.75 (m, 2H), 7.14 (t, J=6.4 Hz, 1H), 7.21 (s, 1H), 7.32 (d, J=7.8 Hz, 1H), 7.60 (t, J=7.6 Hz, 1H), 8.56 (d, J=3.6 Hz, 1H); MS (ESI) m/z 350.7 (M+1)+.

Workup

  1. customThe titled compound was synthesized
  2. customThe crude material was purified by column chromatography
  3. washeluting with mixture of chloroform/ethanol/20% water solution of ammonia (200:10:1)
  4. washthe final product was washed with diethyl ether

Sources & evidence

ORD record
ord-ddb85890747f46fb8ea927465102b1f5
Source dataset
uspto-grants-2016_09
Patent number
US09447051B2

Linked notes

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